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Haloalkanes and Haloarenes question

2012 · Shift 0 · Q12
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Haloalkanes and Haloarenes question

2012 · Shift 0 · Q12

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Iodoform can be prepared from all except :
  1. A
    Ethyl methyl ketone
  2. B
    Isopropyl alcohol
  3. C
    3–Methyl – 2– butanone
  4. D
    Isobutyl alcohol
View written solutionFree

Correct answer: D

  1. Identify the requirement for iodoform reaction

    Iodoform, CHI3\mathrm{CHI_3}CHI3​, is formed by compounds that contain either:

    • a methyl ketone group: RCOCH3\mathrm{RCOCH_3}RCOCH3​, or
    • a secondary alcohol of the type: CH3CH(OH)R\mathrm{CH_3CH(OH)R}CH3​CH(OH)R,

    because such alcohols are oxidized to methyl ketones under the reaction conditions.

  2. Check each option

    Option A: Ethyl methyl ketone

    Ethyl methyl ketone is: CH3COCH2CH3\mathrm{CH_3COCH_2CH_3}CH3​COCH2​CH3​ This has the methyl ketone form RCOCH3\mathrm{RCOCH_3}RCOCH3​.

    Therefore, it gives iodoform test.


    Option B: Isopropyl alcohol

    Isopropyl alcohol is: CH3CH(OH)CH3\mathrm{CH_3CH(OH)CH_3}CH3​CH(OH)CH3​ This is a secondary alcohol of the form CH3CH(OH)R\mathrm{CH_3CH(OH)R}CH3​CH(OH)R.

    On oxidation, it gives acetone: CH3COCH3\mathrm{CH_3COCH_3}CH3​COCH3​ which is a methyl ketone.

    Therefore, it gives iodoform test.


    Option C: 3-Methyl-2-butanone

    Structure: CH3COCH(CH3)CH3\mathrm{CH_3COCH(CH_3)CH_3}CH3​COCH(CH3​)CH3​ This also contains the methyl ketone group RCOCH3\mathrm{RCOCH_3}RCOCH3​.

    Therefore, it gives iodoform test.


    Option D: Isobutyl alcohol

    Isobutyl alcohol is: (CH3)2CHCH2OH\mathrm{(CH_3)_2CHCH_2OH}(CH3​)2​CHCH2​OH This is a primary alcohol, not of the form CH3CH(OH)R\mathrm{CH_3CH(OH)R}CH3​CH(OH)R.

    On oxidation, it forms an aldehyde/acid, not a methyl ketone.

    Therefore, it does not give iodoform test.

  3. Conclusion

    The compound from which iodoform cannot be prepared is: D: Isobutyl alcohol\boxed{\text{D: Isobutyl alcohol}}D: Isobutyl alcohol​

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